1. Field of the Invention
This invention relates to polyfluoroallyloxy compounds, processes for their preparation and copolymers prepared therefrom.
2. Relation to the Prior Art
1. U.S. Pat. No. 2,856,435 to E. S. Lo discloses the preparation of perfluoroallyloxy-1,1-dihydroperfluoroalkanes from 3-chloropentafluoropropene and a 1,1-dihydroperfluoroalkanol in alkaline medium, e.g. ##STR1##
2. U.S. Pat. No. 2,671,799 to W. T. Miller discloses a process for replacing the chlorine in perfluoroallyl chloride (3-chloropentafluoropropene) with methoxy, cyano, iodo and nitrate groups, e.g. EQU CF.sub.2 =CFCF.sub.2 Cl+NaOCH.sub.3 .fwdarw.CF.sub.2 =CFCF.sub.2 OCH.sub.3
3. M. E. Redwood and C. J. Willis, Canad. J. Chem., 45, 389 (1967) describe the reaction of allyl bromide with cesium heptafluoro-2-propoxide to form 2-allyloxyheptafluoropropane: EQU CH.sub.2 =CHCH.sub.2 Br+(CF.sub.3).sub.2 CFO.sup.- Cs.sup.+ .fwdarw.CH.sub.2 =CHCH.sub.2 OCF(CF.sub.3).sub.2 +CsBr
4. J. A. Young, Fluorine Chemistry Reviews, 1, 389-393 (1967) surveys the formation of perfluoroalkoxide anions by the action of alkali metal fluorides on perfluoroketones, perfluoroalkyloxiranes, perfluorocarboxylic acid fluorides and perfluoroalkyl fluorosulfates. References 5-9 which follow are examples of the nucleophilic reactions of perfluoroalkoxide anions.
5. U.S. Pat. No. 3,450,684 to R. A. Darby discloses the preparation of fluorocarbon polyethers and their polymers by reaction of perfluoroalkanoyl fluorides with potassium or quaternary ammonium fluoride and hexafluoropropene epoxide. ##STR2##
6. U.S. Pat. No. 3,674,820 to A. G. Pittman and W. L. Wasley discloses the reaction of fluoroketones with an alkali metal fluoride and an omega-haloalkanoic acid ester to form an omega-(perfluoroalkoxy) alkanoic acid ester, e.g. EQU (CF.sub.3).sub.2 CO+KF+Br(CH.sub.2).sub.4 CO.sub.2 CH.sub.3 .fwdarw.(CF.sub.3).sub.2 CFO(CH.sub.2).sub.4 CO.sub.2 CH.sub.3
7. U.S. Pat. No. 3,795,684 to E. Domba also discloses the reaction of hexafluoroacetone with potassium fluoride and an omega-haloalkanoic acid ester.
8. U.S. Pat. No. 3,527,742 to A. G. Pittman and W. L. Wasley, discloses the reduction of the compounds of Reference 6 to the corresponding alcohols and their esterification to polymerizable acrylates.
9. U.S. Pat. No. 3,799,992 to A. G. Pittman and W. L. Wasley discloses the preparation of (perfluoroalkoxy)vinyl compounds by reaction of a perfluoroketone with an alkali metal fluoride and a 1,2-dihaloethane, followed by dehydrohalogenation of the intermediate 2-perfluoroalkoxyhaloethane. ##STR3##
10. U.S. Pat. No. 3,321,532 to C. E. Lorenz discloses the rearrangement of perfluoro-2-alkoxyalkanoyl fluorides to perfluoroalkoxyolefins by passage over a metal oxide at 100.degree.-400.degree. C., e.g., ##STR4##
11. U.S. Pat. No. 3,467,638 to D. B. Pattison discloses polyfluorovinyl ethers of the formula ##STR5## where n is 1 or 2 and copolymers containing said ethers.
12. L. S. Kobrina, Fluorine Chemistry Reviews, vol. 7, p. 67, Marcel Dekker, Inc., New York (1974), discloses the substitution of hydroxyl into --OC.sub.6 F.sub.5 groups to form --OC.sub.6 F.sub.4 OH.
13. U.S. Pat. No. 4,131,740 to D. C. England discloses the compound ROOC--CF.sub.2 --COF, hexafluoropropane oxide adducts with the formula ##STR6## vinyl ethers prepared from same, of the formula ##STR7## and copolymers prepared from said vinyl ethers; n is 1 to 6, and R is CH.sub.3 or C.sub.2 H.sub.5.
14. U.S. Pat. No. 4,138,426 to D. C. England discloses the nitrile ##STR8## where n is 1 to 6.